NO884270L - Alkadienderivater, deres fremstilling og mellomprodukter til bruk ved fremstillingen. - Google Patents
Alkadienderivater, deres fremstilling og mellomprodukter til bruk ved fremstillingen.Info
- Publication number
- NO884270L NO884270L NO88884270A NO884270A NO884270L NO 884270 L NO884270 L NO 884270L NO 88884270 A NO88884270 A NO 88884270A NO 884270 A NO884270 A NO 884270A NO 884270 L NO884270 L NO 884270L
- Authority
- NO
- Norway
- Prior art keywords
- residue
- ethyl
- dimethylamino
- formula
- hydroxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 52
- 239000013067 intermediate product Substances 0.000 title description 2
- 150000001993 dienes Chemical class 0.000 title 1
- -1 phenoxy, piperidino, dimethylamino Chemical group 0.000 claims description 112
- 238000002360 preparation method Methods 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 150000002081 enamines Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000001261 hydroxy acids Chemical group 0.000 claims description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- QXHXMALPRIXDEU-UHFFFAOYSA-P [3-(dimethylamino)-2-[(dimethylazaniumyl)methyl]prop-2-enyl]-dimethylazanium Chemical compound CN(C)C=C(C[NH+](C)C)C[NH+](C)C QXHXMALPRIXDEU-UHFFFAOYSA-P 0.000 claims description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000012346 acetyl chloride Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 2
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 440
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 219
- 239000000243 solution Substances 0.000 description 187
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 126
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 120
- 238000009835 boiling Methods 0.000 description 116
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 92
- 238000000746 purification Methods 0.000 description 90
- 238000002844 melting Methods 0.000 description 80
- 230000008018 melting Effects 0.000 description 80
- 239000000203 mixture Substances 0.000 description 68
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 68
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 61
- 229910052710 silicon Inorganic materials 0.000 description 61
- 239000010703 silicon Substances 0.000 description 61
- 238000003786 synthesis reaction Methods 0.000 description 48
- 238000004440 column chromatography Methods 0.000 description 46
- 238000001953 recrystallisation Methods 0.000 description 46
- 239000003480 eluent Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- LZMPEVQYFYBCBC-UHFFFAOYSA-N [3-(dimethylamino)-4-ethoxy-4-oxobut-2-enylidene]-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.CCOC(=O)C(\N(C)C)=C\C=[N+](C)C LZMPEVQYFYBCBC-UHFFFAOYSA-N 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 34
- 239000003921 oil Substances 0.000 description 34
- 235000019198 oils Nutrition 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
- LGFXXWMXKUQLNQ-UHFFFAOYSA-N ethyl 5-(dimethylamino)-6-ethoxy-2-phenyl-6-sulfanylidenehexa-2,4-dienoate Chemical compound CCOC(=S)C(N(C)C)=CC=C(C(=O)OCC)C1=CC=CC=C1 LGFXXWMXKUQLNQ-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000012074 organic phase Substances 0.000 description 24
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- RSJVBANROGGYRD-UHFFFAOYSA-N ethyl 2-(dimethylamino)-5-methylsulfanyl-6-oxo-6-phenylhexa-2,4-dienoate Chemical compound CCOC(=O)C(N(C)C)=CC=C(SC)C(=O)C1=CC=CC=C1 RSJVBANROGGYRD-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- WFOPLDPCLHCWRG-UHFFFAOYSA-N o-ethyl 2-phenylethanethioate Chemical compound CCOC(=S)CC1=CC=CC=C1 WFOPLDPCLHCWRG-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- PBSSYSNVKZYEAB-UHFFFAOYSA-N ethyl 2-[(4-methylphenyl)methylsulfanyl]acetate Chemical compound CCOC(=O)CSCC1=CC=C(C)C=C1 PBSSYSNVKZYEAB-UHFFFAOYSA-N 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 10
- ZBFSNFYOLZFPEU-UHFFFAOYSA-N 1-phenylpropane-1-thione Chemical compound CCC(=S)C1=CC=CC=C1 ZBFSNFYOLZFPEU-UHFFFAOYSA-N 0.000 description 9
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 8
- YKZOSZJGWANIJI-UHFFFAOYSA-N 5-(dimethylamino)-6-oxo-2-phenyl-6-sulfanylhexa-2,4-dienoic acid Chemical compound CN(C)C(=CC=C(C1=CC=CC=C1)C(=O)O)C(=O)S YKZOSZJGWANIJI-UHFFFAOYSA-N 0.000 description 7
- 239000010502 orange oil Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 235000019502 Orange oil Nutrition 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- SAXAKBZGZUALJN-UHFFFAOYSA-N ethyl 2-(3-phenoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1 SAXAKBZGZUALJN-UHFFFAOYSA-N 0.000 description 5
- DSQYZRGDWNCXMM-UHFFFAOYSA-N ethyl 2-(dimethylamino)-4-(1-oxo-3,4-dihydronaphthalen-2-ylidene)but-2-enoate Chemical compound C1=CC=C2C(=O)C(=CC=C(C(=O)OCC)N(C)C)CCC2=C1 DSQYZRGDWNCXMM-UHFFFAOYSA-N 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- JZLMLFCJWFMZMC-UHFFFAOYSA-N 3-phenylpropanethioic s-acid Chemical compound SC(=O)CCC1=CC=CC=C1 JZLMLFCJWFMZMC-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- GTCBVGDJIQFBFF-AATRIKPKSA-N ethyl (e)-4-(dimethylamino)-2-oxobut-3-enoate Chemical compound CCOC(=O)C(=O)\C=C\N(C)C GTCBVGDJIQFBFF-AATRIKPKSA-N 0.000 description 4
- CEMPSFNCGGPTDC-UHFFFAOYSA-N ethyl 2-butyl-5-(dimethylamino)-6-ethoxy-6-sulfanylidenehexa-2,4-dienoate Chemical compound CCCCC(C(=O)OCC)=CC=C(N(C)C)C(=S)OCC CEMPSFNCGGPTDC-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- ZKKZMHOWOZFGER-UHFFFAOYSA-N o-ethyl 5-(dimethylamino)-2,5-diphenylpenta-2,4-dienethioate Chemical compound C=1C=CC=CC=1C(C(=S)OCC)=CC=C(N(C)C)C1=CC=CC=C1 ZKKZMHOWOZFGER-UHFFFAOYSA-N 0.000 description 4
- NOVVNMZMNDCXRJ-UHFFFAOYSA-N o-ethyl hexanethioate Chemical compound CCCCCC(=S)OCC NOVVNMZMNDCXRJ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 3
- GMNHNZHVFJFQDZ-UHFFFAOYSA-N 2-bromo-1-(2,2-dimethyl-1,3-benzodioxol-5-yl)ethanone Chemical compound C1=C(C(=O)CBr)C=C2OC(C)(C)OC2=C1 GMNHNZHVFJFQDZ-UHFFFAOYSA-N 0.000 description 3
- QMJWPWCKRKHUNY-UHFFFAOYSA-N 2-phenylsulfanylacetonitrile Chemical compound N#CCSC1=CC=CC=C1 QMJWPWCKRKHUNY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- BHNSIAVRHHJDGU-UHFFFAOYSA-N C=1C=CC=CC=1C(C(=O)S)C1CCCCC1 Chemical compound C=1C=CC=CC=1C(C(=O)S)C1CCCCC1 BHNSIAVRHHJDGU-UHFFFAOYSA-N 0.000 description 3
- GCFWDKMXLHOULO-UHFFFAOYSA-N O-ethyl 4-phenylbutanethioate Chemical compound C1(=CC=CC=C1)CCCC(OCC)=S GCFWDKMXLHOULO-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- WWPDTQFHNCQJDA-UHFFFAOYSA-N [(z)-3-(dimethylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobut-2-enylidene]-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.C[N+](C)=C\C=C(N(C)C)\C(=O)OC(C)(C)C WWPDTQFHNCQJDA-UHFFFAOYSA-N 0.000 description 3
- YVNRSAQYBRNZOL-UHFFFAOYSA-N [3-(dimethylamino)-3-phenylprop-2-enylidene]-dimethylazanium;tetrafluoroborate Chemical compound F[B-](F)(F)F.C[N+](C)=C\C=C(N(C)C)\C1=CC=CC=C1 YVNRSAQYBRNZOL-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 3
- 238000011097 chromatography purification Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- FZFDCLTWPJAREZ-UHFFFAOYSA-N diethyl 2-(3-benzoylphenyl)-5-(dimethylamino)hexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 FZFDCLTWPJAREZ-UHFFFAOYSA-N 0.000 description 3
- ZOLWRICCTHKMNK-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-(3-phenylphenyl)hexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)C1=CC=CC(C=2C=CC=CC=2)=C1 ZOLWRICCTHKMNK-UHFFFAOYSA-N 0.000 description 3
- XTIPXJLQQXEXRM-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-(4-methoxyphenyl)sulfanylhexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)SC1=CC=C(OC)C=C1 XTIPXJLQQXEXRM-UHFFFAOYSA-N 0.000 description 3
- HBFNRBSSZANBKF-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-[(2,4,6-trimethylphenyl)methylsulfanyl]hexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)SCC1=C(C)C=C(C)C=C1C HBFNRBSSZANBKF-UHFFFAOYSA-N 0.000 description 3
- CGWHZDCWVTVQRG-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-[(2-methylphenyl)methylsulfanyl]hexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)SCC1=CC=CC=C1C CGWHZDCWVTVQRG-UHFFFAOYSA-N 0.000 description 3
- ZICLLENKIBIDJN-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-[(3-methylphenyl)methylsulfanyl]hexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)SCC1=CC=CC(C)=C1 ZICLLENKIBIDJN-UHFFFAOYSA-N 0.000 description 3
- GPGIHZKJHMJGDO-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-[(4-phenylphenyl)methylsulfanyl]hexa-2,4-dienedioate Chemical compound C1=CC(CSC(C(=O)OCC)=CC=C(N(C)C)C(=O)OCC)=CC=C1C1=CC=CC=C1 GPGIHZKJHMJGDO-UHFFFAOYSA-N 0.000 description 3
- KGWRXJDKWLEHBZ-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-naphthalen-1-ylhexa-2,4-dienedioate Chemical compound C1=CC=C2C(C(C(=O)OCC)=CC=C(C(=O)OCC)N(C)C)=CC=CC2=C1 KGWRXJDKWLEHBZ-UHFFFAOYSA-N 0.000 description 3
- BCXXEXSQVLCXDV-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-naphthalen-2-ylsulfanylhexa-2,4-dienedioate Chemical compound C1=CC=CC2=CC(SC(C(=O)OCC)=CC=C(N(C)C)C(=O)OCC)=CC=C21 BCXXEXSQVLCXDV-UHFFFAOYSA-N 0.000 description 3
- PBTLNUCQGLMNKY-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-octylhexa-2,4-dienedioate Chemical compound CCCCCCCCC(C(=O)OCC)=CC=C(N(C)C)C(=O)OCC PBTLNUCQGLMNKY-UHFFFAOYSA-N 0.000 description 3
- GBALWEVJTZJQAQ-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-phenylhexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)C1=CC=CC=C1 GBALWEVJTZJQAQ-UHFFFAOYSA-N 0.000 description 3
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- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
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- 230000005494 condensation Effects 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
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- NPGCJASUICIRAD-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-[(4-propan-2-ylphenyl)methylsulfanyl]hexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)SCC1=CC=C(C(C)C)C=C1 NPGCJASUICIRAD-UHFFFAOYSA-N 0.000 description 2
- MTZBQJOBUVSRFX-UHFFFAOYSA-N diethyl 2-(dimethylamino)-5-[[4-(trifluoromethyl)phenyl]methylsulfanyl]hexa-2,4-dienedioate Chemical compound CCOC(=O)C(N(C)C)=CC=C(C(=O)OCC)SCC1=CC=C(C(F)(F)F)C=C1 MTZBQJOBUVSRFX-UHFFFAOYSA-N 0.000 description 2
- BPWXUGSFTGIXBQ-UHFFFAOYSA-N diethyl 2-benzylsulfanyl-5-hydroxyhexa-2,4-dienedioate Chemical compound CCOC(=O)C(O)=CC=C(C(=O)OCC)SCC1=CC=CC=C1 BPWXUGSFTGIXBQ-UHFFFAOYSA-N 0.000 description 2
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- 229940079593 drug Drugs 0.000 description 2
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- QBJLBJGROLHCBL-UHFFFAOYSA-N ethyl 2-(dimethylamino)-4-(2-oxo-3h-inden-1-ylidene)but-2-enoate Chemical compound C1=CC=C2C(=CC=C(C(=O)OCC)N(C)C)C(=O)CC2=C1 QBJLBJGROLHCBL-UHFFFAOYSA-N 0.000 description 2
- KMQANNFZVZJFSI-UHFFFAOYSA-N ethyl 2-(dimethylamino)-4-(4-oxo-1H-isothiochromen-3-ylidene)but-2-enoate Chemical compound C1=CC=C2C(=O)C(=CC=C(C(=O)OCC)N(C)C)SCC2=C1 KMQANNFZVZJFSI-UHFFFAOYSA-N 0.000 description 2
- XDPQKEDRHVODOM-UHFFFAOYSA-N ethyl 2-(dimethylamino)-5-methylsulfanyl-6-naphthalen-2-yl-6-oxohexa-2,4-dienoate Chemical compound C1=CC=CC2=CC(C(=O)C(SC)=CC=C(C(=O)OCC)N(C)C)=CC=C21 XDPQKEDRHVODOM-UHFFFAOYSA-N 0.000 description 2
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- BKVPKIQKMWLUIQ-UHFFFAOYSA-N ethyl 5-(dimethylamino)-6-ethoxy-2-methyl-6-sulfanylidenehexa-2,4-dienoate Chemical compound CCOC(=O)C(C)=CC=C(N(C)C)C(=S)OCC BKVPKIQKMWLUIQ-UHFFFAOYSA-N 0.000 description 2
- GZVCAXYHFMVKDO-UHFFFAOYSA-N ethyl 5-oxo-5-phenyl-2-phenylsulfanylpent-2-enoate Chemical compound C=1C=CC=CC=1C(=O)CC=C(C(=O)OCC)SC1=CC=CC=C1 GZVCAXYHFMVKDO-UHFFFAOYSA-N 0.000 description 2
- KRQJUSSTNHGGFK-UHFFFAOYSA-N ethyl 6-(4-bromophenyl)-2-(dimethylamino)-5-methylsulfanyl-6-oxohexa-2,4-dienoate Chemical compound CCOC(=O)C(N(C)C)=CC=C(SC)C(=O)C1=CC=C(Br)C=C1 KRQJUSSTNHGGFK-UHFFFAOYSA-N 0.000 description 2
- RNDVIILZYOIDBF-UHFFFAOYSA-N ethyl 6-ethoxy-5-hydroxy-2-phenyl-6-sulfanylidenehexa-2,4-dienoate Chemical compound CCOC(=S)C(O)=CC=C(C(=O)OCC)C1=CC=CC=C1 RNDVIILZYOIDBF-UHFFFAOYSA-N 0.000 description 2
- UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000004761 fibrosis Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NABIEUDJTRZGMY-UHFFFAOYSA-N o-ethyl 5-(dimethylamino)-5-phenyl-2-(2-phenylethyl)penta-2,4-dienethioate Chemical compound C=1C=CC=CC=1C(N(C)C)=CC=C(C(=S)OCC)CCC1=CC=CC=C1 NABIEUDJTRZGMY-UHFFFAOYSA-N 0.000 description 2
- BRFHVJSHXCMWDB-UHFFFAOYSA-N o-ethyl 5-(dimethylamino)-6-oxo-2,6-diphenylhexa-2,4-dienethioate Chemical compound C=1C=CC=CC=1C(C(=S)OCC)=CC=C(N(C)C)C(=O)C1=CC=CC=C1 BRFHVJSHXCMWDB-UHFFFAOYSA-N 0.000 description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YVZKICWRYOHMRD-UHFFFAOYSA-N tert-butyl 2-oxopropanoate Chemical compound CC(=O)C(=O)OC(C)(C)C YVZKICWRYOHMRD-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- XRJMOKYZZABFPA-UHFFFAOYSA-N ethyl 2-butyl-6-ethoxy-5-hydroxy-6-sulfanylidenehexa-2,4-dienoate Chemical compound CCCCC(C(=O)OCC)=CC=C(O)C(=S)OCC XRJMOKYZZABFPA-UHFFFAOYSA-N 0.000 description 1
- YWYFAAKDVLMGCS-UHFFFAOYSA-N ethyl 2-hydroxy-4-(2-oxo-3h-inden-1-ylidene)but-2-enoate Chemical compound C1=CC=C2C(=CC=C(O)C(=O)OCC)C(=O)CC2=C1 YWYFAAKDVLMGCS-UHFFFAOYSA-N 0.000 description 1
- PSYWMKOWCSEJFM-UHFFFAOYSA-N ethyl 5-acetyloxy-6-ethoxy-2-phenyl-6-sulfanylidenehexa-2,4-dienoate Chemical compound CCOC(=S)C(OC(C)=O)=CC=C(C(=O)OCC)C1=CC=CC=C1 PSYWMKOWCSEJFM-UHFFFAOYSA-N 0.000 description 1
- ONSHSRBFCWCHEP-UHFFFAOYSA-N ethyl 5-cyano-2-hydroxy-5-phenylpenta-2,4-dienoate Chemical compound CCOC(=O)C(O)=CC=C(C#N)C1=CC=CC=C1 ONSHSRBFCWCHEP-UHFFFAOYSA-N 0.000 description 1
- GGLKSHZEJFLBDL-UHFFFAOYSA-N ethyl 6-(3-chlorophenyl)-2-(dimethylamino)-5-methylsulfanyl-6-oxohexa-2,4-dienoate Chemical compound CCOC(=O)C(N(C)C)=CC=C(SC)C(=O)C1=CC=CC(Cl)=C1 GGLKSHZEJFLBDL-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexadiene group Chemical group C=CC=CCC AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8713357A FR2621038B1 (fr) | 1987-09-28 | 1987-09-28 | Derives d'alcadienes, leurs preparations, les medicaments les contenant et produits intermediaires |
Publications (2)
Publication Number | Publication Date |
---|---|
NO884270D0 NO884270D0 (no) | 1988-09-27 |
NO884270L true NO884270L (no) | 1989-03-29 |
Family
ID=9355276
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO88884270A NO884270L (no) | 1987-09-28 | 1988-09-27 | Alkadienderivater, deres fremstilling og mellomprodukter til bruk ved fremstillingen. |
Country Status (18)
Country | Link |
---|---|
US (2) | US4886835A (pt) |
EP (2) | EP0310484A1 (pt) |
JP (1) | JPH01106839A (pt) |
KR (1) | KR890005046A (pt) |
AU (1) | AU611480B2 (pt) |
DK (1) | DK536488A (pt) |
FI (1) | FI884424A (pt) |
FR (1) | FR2621038B1 (pt) |
HU (1) | HU200740B (pt) |
IL (1) | IL87856A0 (pt) |
MA (1) | MA21385A1 (pt) |
NO (1) | NO884270L (pt) |
NZ (1) | NZ226337A (pt) |
OA (1) | OA08957A (pt) |
PH (1) | PH24992A (pt) |
PT (1) | PT88616A (pt) |
TN (1) | TNSN88097A1 (pt) |
ZA (1) | ZA887211B (pt) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3789100T2 (de) * | 1986-12-26 | 1994-05-19 | Teijin Ltd | Aromatische Derivate und ihre Herstellungsweise. |
US5158943A (en) * | 1988-11-21 | 1992-10-27 | Takeda Chemical Industries, Ltd. | Sulfur-containing heterocyclic compounds |
NZ231939A (en) * | 1988-12-28 | 1991-07-26 | Takeda Chemical Industries Ltd | Benzothiopyran derivatives and medicaments |
DE19632093C1 (de) * | 1996-08-08 | 1997-09-04 | Siemens Ag | Voll differentieller Digital-Analog-Wandler mit geringer Anzahl von Widerständen |
US6486210B2 (en) * | 2000-04-14 | 2002-11-26 | Temple University—Of the Commonwealth System of Higher Education | Substituted styryl benzylsulfones for treating proliferative disorders |
JP3973941B2 (ja) * | 2002-03-25 | 2007-09-12 | 富士フイルム株式会社 | δ−アミノペンタジエン酸エステル誘導体の製造方法 |
JP2008520683A (ja) * | 2004-11-18 | 2008-06-19 | ジ インスチチュート フォー ファーマシューティカル ディスカバリー、エルエルシー | タンパク質チロシンホスファターゼ阻害剤としてのヘテロシクリルビフェニル誘導体 |
JP5078386B2 (ja) * | 2006-05-08 | 2012-11-21 | 株式会社Adeka | 新規化合物、該化合物を用いた光学フィルター及び光学記録材料 |
AU2010241567B2 (en) | 2009-04-29 | 2013-10-31 | Amarin Pharmaceuticals Ireland Limited | Pharmaceutical compositions comprising EPA and a cardiovascular agent and methods of using the same |
WO2013012998A1 (en) | 2011-07-19 | 2013-01-24 | Emory University | Tak1 kinase inhibitors, compositions, and used related thereto |
KR101603324B1 (ko) * | 2013-10-11 | 2016-03-14 | 주식회사 엘지생명과학 | 3-알킬티오-2-브로모피리딘 화합물의 제조방법 |
CN110483352B (zh) * | 2019-09-04 | 2021-03-16 | 中南大学 | 一种硫氨酯与苄基硫醚基乙酸的联产方法及其在浮选中的应用 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4619945A (en) * | 1985-10-09 | 1986-10-28 | Usv Pharmaceutical Corp | Polyene compounds useful in the treatment of allergic responses |
ATE53009T1 (de) * | 1985-12-17 | 1990-06-15 | Wellcome Found | Schaedlingsbekaempfende dihalovinylalkenylamide. |
DK435087A (da) * | 1986-09-10 | 1988-03-11 | Hoffmann La Roche | Isoprenderivater |
-
1987
- 1987-09-28 FR FR8713357A patent/FR2621038B1/fr not_active Expired
-
1988
- 1988-09-26 US US07/248,720 patent/US4886835A/en not_active Expired - Fee Related
- 1988-09-26 EP EP88402416A patent/EP0310484A1/fr not_active Withdrawn
- 1988-09-26 NZ NZ226337A patent/NZ226337A/xx unknown
- 1988-09-26 EP EP90121043A patent/EP0418933A1/fr not_active Withdrawn
- 1988-09-26 ZA ZA887211A patent/ZA887211B/xx unknown
- 1988-09-26 MA MA21630A patent/MA21385A1/fr unknown
- 1988-09-27 KR KR1019880012463A patent/KR890005046A/ko not_active Application Discontinuation
- 1988-09-27 IL IL87856A patent/IL87856A0/xx unknown
- 1988-09-27 JP JP63239869A patent/JPH01106839A/ja active Pending
- 1988-09-27 NO NO88884270A patent/NO884270L/no unknown
- 1988-09-27 FI FI884424A patent/FI884424A/fi not_active Application Discontinuation
- 1988-09-27 TN TNTNSN88097A patent/TNSN88097A1/fr unknown
- 1988-09-27 HU HU885027A patent/HU200740B/hu not_active IP Right Cessation
- 1988-09-27 PH PH37598A patent/PH24992A/en unknown
- 1988-09-27 DK DK536488A patent/DK536488A/da not_active Application Discontinuation
- 1988-09-28 AU AU22934/88A patent/AU611480B2/en not_active Expired - Fee Related
- 1988-09-28 PT PT88616A patent/PT88616A/pt not_active Application Discontinuation
- 1988-09-28 OA OA59440A patent/OA08957A/xx unknown
-
1989
- 1989-07-19 US US07/381,825 patent/US4971979A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR890005046A (ko) | 1989-05-11 |
PH24992A (en) | 1990-12-26 |
HUT48191A (en) | 1989-05-29 |
ZA887211B (en) | 1989-05-30 |
OA08957A (fr) | 1990-11-30 |
US4971979A (en) | 1990-11-20 |
FI884424A (fi) | 1989-03-29 |
AU2293488A (en) | 1989-04-06 |
IL87856A0 (en) | 1989-03-31 |
US4886835A (en) | 1989-12-12 |
EP0310484A1 (fr) | 1989-04-05 |
PT88616A (pt) | 1989-07-31 |
HU200740B (en) | 1990-08-28 |
NZ226337A (en) | 1990-06-26 |
DK536488A (da) | 1989-03-29 |
EP0418933A1 (fr) | 1991-03-27 |
FR2621038B1 (fr) | 1989-12-29 |
AU611480B2 (en) | 1991-06-13 |
FR2621038A1 (fr) | 1989-03-31 |
FI884424A0 (fi) | 1988-09-27 |
MA21385A1 (fr) | 1989-04-01 |
JPH01106839A (ja) | 1989-04-24 |
NO884270D0 (no) | 1988-09-27 |
TNSN88097A1 (fr) | 1990-07-10 |
DK536488D0 (da) | 1988-09-27 |
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